This major research paper (MRP) analyzes the potential of bell hooks’s notion of learning communities within the context of contemporary arts institutions in the city of Toronto. It considers how two public programs—the roundtable discussion "Ways of Caring" at the Art Gallery of Ontario and the public gathering by BUSH gallery, "Beach(fire) Blanket Bingo Biennial", presented by the Toronto Biennial of Art—created learning environments that engaged participants in critical thinking, dialogue and self-reflexive practice. In doing so, each event challenged the colonial impositions and constructs of the host institution while subverting the structures that exclude racialized communities from their narratives. The MRP examines the diverse means through which learning communities take form, following three categories of analysis: ritualistic impositions, as discussed by Carol Duncan; participation and collective agency in relation to the writings of Claire Bishop, Pablo Helguera, and Irit Rogoff; and lastly, learning communities, as articulated by bell hooks. The essay ultimately seeks to prove that, by engaging in radical pedagogical approaches, museum education and discursive programs can challenge the institution’s colonial histories and structures by prioritizing and amplifying the voices of BIPOC communities.